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Synthesis and Cytotoxic Activity of Novel C-23-Modified Asiatic Acid Derivatives.

ABSTRACT: We selectively oxidized the C-23 hydroxyl group in an asiatic acid (AA) derivative and then, for the first time with AA, modification of the C-23 carboxyl group was conducted to synthesize a series of new AA derivatives. The evaluation of their cytotoxic activities against two human cancer cell lines (SKOV-3 and HCT116) using the MTT assay in vitro revealed a distinctive structure activity relationship (SAR) associated with the intramolecular hydrogen bonding of the amide moiety at C-23. According to the established SAR, the cytotoxic activities of four promising compounds were then evaluated against MCF-7, A549, A2780, HepG2 and HL-60 cancer cell lines. Compound 10 had the best cytotoxic activity among all tested derivatives in the HL-60 cell line, giving IC50 = 0.47 ?M, while showing no cytotoxic effect against human normal cells (HUVEC).

SUBMITTER: Lu YH

PROVIDER: S-EPMC7464201 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Synthesis and Cytotoxic Activity of Novel C-23-Modified Asiatic Acid Derivatives.

Lu Yi-Hong YH Chen Ming-Cang MC Liu Fang F Xu Zhou Z Tian Xiao-Ting XT Xie Yang Y Huang Cheng-Gang CG

Molecules (Basel, Switzerland) 20200814 16

We selectively oxidized the C-23 hydroxyl group in an asiatic acid (AA) derivative and then, for the first time with AA, modification of the C-23 carboxyl group was conducted to synthesize a series of new AA derivatives. The evaluation of their cytotoxic activities against two human cancer cell lines (SKOV-3 and HCT116) using the MTT assay in vitro revealed a distinctive structure activity relationship (SAR) associated with the intramolecular hydrogen bonding of the amide moiety at C-23. Accordi ...[more]

PMID: 32823913

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